ByGrant Hermanns, writer at
I know way too much about movies, my mind is like a walking IMDB, only not perfect. Don't forget to hit up my Twitter: @grantheftautho
Grant Hermanns

It's hard to believe the former Saturday Night Live actor is not even 40 years old yet, but the comedy star has put out a lot of work in his 38 years. He formed a comedy group with two childhood friends that got them onto SNL and made them stars, increasing popularity thanks to Lonely Island's songs and crazy characters. Samberg lasted seven years on the series before scoring roles in movies and a new TV show that led to his exit.

In honor of the actor's birthday, let's take a look back at Samberg's best characters over the years.

Conner4Real — Popstar: Never Stop Never Stopping

Popstar was Samberg's second starring collaboration with his comedy group, not only starring alongside Jorma Taccone and Akiva Schaffer, but also co-wroting it with them, which resulted in one of thte most outrageous and funniest characters in his career. While promoting the film, he appeared as the character on the Season 41 finale of SNL, debuting the track "Finest Girls" from the film.

Intended to be a parody of various pop stars — primarily Justin Bieber — Conner's no-filter attitude and NSFW songs were perfect for Samberg, who ran with the character and made him truly memorable. Here's the hilariously NSFW version of the song "Finest Girls" from Popstar:

Ballad Singer — Saturday Night Live

This character doesn't technically have a name, but he has made three total performances on SNL alongside Justin Timberlake, and each one was more memorable than the last. The ballad singers made their debut in Season 33 of the sketch series with the classic song "Dick in a Box," which won the Creative Arts Emmy Award for Outstanding Music & Lyrics.

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The two would reunite two years later for the hit song "Motherlover," in which the pair are released from prison just in time for Mother's Day and in struggling to get a gift, decide that they're perfect for each other's mothers. The duo would come together once more for "3 Way (The Golden Rule)," which also featured Lady Gaga and earned an Emmy nomination for Outstanding Music & Lyrics. The sheer bizarre nature that goes into the character's logic is hilarious and makes him one to remember. Here's the slightly-NSFW hit conclusion to the ballad trilogy, "3 Way":

Jake Peralta — Brooklyn Nine-Nine

Shortly after leaving SNL, Andy Samberg returned to television to star in the police comedy Brooklyn Nine-Nine as Jake Peralta, the star detective of the precinct who's also quite a fool at the same time. His childish antics and wild behavior make him one of the best characters in the ensemble series, and one of Samberg's most memorable. Here's a compilation of some of Peralta's best scenes from Season 1, which includes some other great characters:

Brent McHale — Cloudy With A Chance Of Meatballs 1 & 2

Yes, technically, McHale is an animated character, but that doesn't take away from the quality comedy that comes from Samberg in the role. The Cloudy character that was once a childhood star still living off of his fame is the perfect amount of zany for Samberg and if it had been a live-action film, he would have done just as well. Here's one of the funniest Brent moments from the first Cloudy movie:

Jesse Abrams — Celeste and Jesse Forever

This is a character that flies under the radar for many fans, as it was both an independent movie and a dramedy. The thing I personally loved about Celeste and Jesse was that it offered Samberg a chance to be a more diverse actor, providing plenty of comedy in the role when needed but with the perfect amount of dramatic touch. Here's the trailer for the funny — yet heartbreaking — film:

Rod Kimble — Hot Rod

Samberg's debut performance on the big screen was also one of his best characters, with Rod "Hot Rod" Kimble going down in history as the best — and worst — stuntman the world has ever seen. While the film might not have been the best of his work, the title character certainly was, his offbeat humor, never-ending devotion and amateurish attempts truly making it hard to ever forget the legend that it "Hot Rod." Here's a compilation of some of Rod's best moments from the film, along with the supporting characters:

Nicolas Cage — Saturday Night Live

Whenever actors get hired for SNL, it almost seems like it's a requirement to be able to perform a celebrity impression. Samberg filled out a number of celebrity characters through his years on the series, but one of his funniest and perfect was of actor Nicolas Cage.

Not only did he get the look down, he also did a great job of impersonating the actor's demeanor and voice. His great impression makes his version of the character one of the best he's ever portrayed. Here's a clip of Samberg playing Nicolas Cage alongside Bradley Cooper:

Shy Ronnie — Saturday Night Live

Shy Ronnie was actually one of the few SNL digital shorts Samberg starred in that wasn't written by his comedy group, The Lonely Island. Music producer Rick tha Rular submitted some tracks to the group in 2008, and the first "Shy Ronnie" song was from one of the tracks Rular sent in. Not only did the song — which earned an Emmy nomination for Outstanding Original Music & Lyrics — and its sequel, "Ronnie & Clyde," feature a really good tune, but the video also starred Samberg as another hilarious character, Shy Ronnie.

What's really great about this character is that in both songs, he's working alongside Rihanna and acts shy and mumbles on the mic when she's near, but when she leaves he breaks into a full rap that clearly goes against his character. Samberg does such a great job of going from quiet to in-your-face lyrics that this truly makes Ronnie one of his best characters. Here's the second Shy Ronnie song, "Ronnie & Clyde":

The Boss — Saturday Night Live

Technically, this character is addressed at the beginning of the video as Mr. Samberg, but the actor still plays quite the character of "The Boss" in the SNL digital short performed by Samberg and The Lonely Island. Samberg's depiction of a normal day starting off with promoting synergy and eating bagels and ending with flying into the sun propelled him to be one of the funniest characters he's played — as well as one of the most popular of his career, earning close to 144 million views on YouTube for the song. Here's the hilarious and NSFW depiction of what being a boss is like:

The Hipster — Saturday Night Live

There is no other real way to describe the character in the "Threw It On The Ground" as the Hipster, a man obsessed with living outside of "the system," throwing anything on the ground he deems against his moral values or against regular logic. This crazy character became a viral hit after the video aired, resulting in yet another hilarious performance from Samberg. Here's the destructive video:

Creep 1 — Saturday Night Live

The Lonely Island were hitting their peak when they created "The Creep," a song about a dance move that makes you look like someone you'd walk in the opposite direction from no matter where you are. The trio did a great job with both the lyrics and the look for the song, but of the three performers' solo verses, Samberg's might've been the funniest and the creepiest at the same time. He knew how to deliver his weird story with such a wacky energy that makes this an unforgettable character. Here's the video for the hilariously creepy dance:

Which is your favorite Andy Samberg character? Did they make it on this list? Let us know in the comments below!


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